4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Base Information

Chemical Name:4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine
CAS No.:1261154-08-8
Molecular Formula:C₂₇H₂₇BrNO₇P
Molecular Weight:588.392
Hs Code.:

Synonyms:4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

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Chemical Property of 4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

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Technology Process of 4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

There total 11 articles about 4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

: 1261154-07-7
4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine methyl ester

: 1261154-08-8
4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Guidance literature:: 4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine methyl ester; With lithium hydroxide; In tetrahydrofuran; water; for 0.5h; Cooling with ice;

With hydrogenchloride; In water; pH=2;
DOI:10.1016/j.bmc.2010.09.040

Reference yield:

: 60-18-4,18875-48-4,25619-78-7,30704-25-7
L-tyrosine

: 1261154-08-8
4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Guidance literature:: Multi-step reaction with 11 steps

1.1: thionyl chloride / 0.08 h / 0 °C / Inert atmosphere

1.2: 21 h / 0 - 20 °C

2.1: sodium carbonate / water; acetone / 3 h / 20 °C

3.1: triethylamine / acetonitrile / 3 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 8 h / 60 °C / Inert atmosphere

5.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h

7.1: cesium fluoride / 1 h

8.1: hydrogen / palladium on activated charcoal / methanol / 6 h / 20 °C / Inert atmosphere

9.1: sodium hydrogencarbonate / acetonitrile; water / 20 °C

10.1: sulfurous dibromide / pyridine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice; sealed flask

11.1: water; lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice

11.2: pH 2

With sulfurous dibromide; thionyl chloride; dimethylsulfide borane complex; water; hydrogen; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; cesium fluoride; lithium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium on activated charcoal; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;

Reference yield:

: 183021-88-7
methyl 2-{[(benzyloxy)carbonyl]amino}-3-(4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)propanoate

: 1261154-08-8
4-[(dimethyloxyphosphinyl)-bromomethyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-phenylalanine

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 8 h / 60 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 20 °C / Cooling with ice

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h

4.1: cesium fluoride / 1 h

5.1: hydrogen / palladium on activated charcoal / methanol / 6 h / 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate / acetonitrile; water / 20 °C

7.1: sulfurous dibromide / pyridine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice; sealed flask

8.1: water; lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Cooling with ice

8.2: pH 2

With sulfurous dibromide; dimethylsulfide borane complex; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; cesium fluoride; lithium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium on activated charcoal; palladium diacetate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;